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Pyridine → HCID 178490724, Verbindung

HRID 2241170
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2241170
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:27])[NH:25][OH:26])=[CH:20][CH:19]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.[S:39](Cl)(Cl)=[O:40]>O1CCCC1.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[NH:27][S:39](=[O:40])[O:26][N:25]=3)=[CH:22][CH:23]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1
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Komponenten

6

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 1784907253-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide

Produkt 1

HCID 178490724HCID 178490724, VerbindungAusbeute 9,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide (110 mg, 0.23 mmol) in tetrahydrofuran (7.0 ml) under argon was treated with pyridine (37 mg, 2 equiv.) and cooled to 0° C. A solution of thionyl chloride (28 mg, 1.01 equiv.) in dichloromethane (1.0 ml) was then added dropwise in 6 min. The mixture was stirred at 0° C. for 20 min and then at room temperature for 45 min. The solvent was evaporated and the residue diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated. Purification via preparative HPLC (Column: ZORBAX ECLIPSE XDB-C18, 21.2×50 mm, 5 um, PN 970050-902, SN USDN001082. Gradient: 0-1.2 min: 10% CH3 CN in (water+0.1% HCO2H), 1.2-4.7 min: increasing of CH3CN from 10% to 95%, 4.7-5.7 min: 95% of CH3CN, 5.7-59 min: decreasing of CH3CN from 95% to 10%. Program end at 6 min. Flow:30 ml/min) yielded the title compound as a light green solid (11 mg, 9%), MS (ISP): m/e=519.1 (M−H).

Aufarbeitung

  1. waitat room temperature for 45 min
  2. customThe solvent was evaporated
  3. additionthe residue diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated
  7. customPurification
  8. temperaturevia preparative HPLC (Column: ZORBAX ECLIPSE XDB-C18, 21.2×50 mm, 5 um, PN 970050-902, SN USDN001082. Gradient: 0-1.2 min: 10% CH3 CN in (water+0.1% HCO2H), 1.2-4.7 min: increasing of CH3CN from 10% to 95%, 4.7-5.7 min: 95% of CH3CN, 5.7-59 min: decreasing of CH3CN from 95% to 10%. Program end at 6 min. Flow:30 ml/min)

Quellen und Nachweise

ORD-Eintrag
ord-744b0d4a329f4931b65659aea1e35cc2
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723538B2

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